3-Methoxyaniline → N-(3-methoxyphenyl)-3-phenylprop-2-enamide

Participants

Reaction Steps

A solution of cinnamoyl chloride (4.25 g, 25.6 mmol) in acetone (25 mL) was added to a solution of 3-methoxyaniline (2.74 mL, 24.4 mmol) and anhydrous K2CO3 (3.7 g, 26.8 mmol) in acetone-ice (28 mL-28 g) and the resulting reaction mixture was stirred at rt for 3 h. The reaction mixture was then poured into ice water, filtered, and washed with water. Recrystallization from EtOH gave N-(3-methoxyphenyl)cinnamamide (intermediate 13) (4.56 g, 74%) as a white solid.

Provenance & Evidence